Open chain allyl citrylidene acetone



Patented Aug. 25, 1936 UNITED STATES PATENT OFFICE OPEN CHAIN ALLYLGITRYLIDENE ACETO No Drawing.

Original application September 18, 1930, Serial No. 482,906. Divided andthis application December 28, 1932, Serial No.

1 Claim.

This invention relates to the open chain condensation product of citraland allyl acetone in the presence of alkaline condensation agents, andis a division of my copending application, Serial No. 482,906, filedSeptember 18, 1930.

Heretoiore, compounds known as open chain ionones have been obtained bycondensing citral with acetone. The object of the present invention isto provide a new compound of this general type, and a process ofobtaining same.

According to the present invention citral is treated with allyl acetonein the presence of an alkaline condensing agent to form allylcitrylidene acetone, an open chain compound having the followingformula:

This heretofore unknown compound is a liquid having a boiling pointbetween 140 to 150 C. at 3 mm. pressure, has a specific gravity of.9070, is

insoluble in water, and soluble in most of the usual organic solvents.It may be used as a starting material in the preparation of othercompounds, such as allyl cyclo citrylidene acetone.

The reaction may be represented as follows:

(1) C(OH:;)z=CH-CHz-CHr-C(CH3)=CHCHO+ (citral) CHrGOOHzCHzCH=CH2alkaline (allyl acetone) condensing agent Example:12 kilos of citral and'7 kilos of allyl acetone are agitated with 680 gms. of sodium 211- 10coholate for about an hour at room temperature. The mixture isneutralized and the layer of unreacted allyl'acetone and citralseparated. The remainder of the mixture is then distilled at 140-170" C.and 10 mm. pressure. Allyl citrylidene 5 acetone is thus obtained.

The proportions of reactants as given above are merely illustrative andmay be varied considerably. In place of sodium alcoholate other alkalinecondensing agents may be used, such as 20 caustic soda, sodium amide.

I claim as my invention:

As a new compound, open chain allyl citrylidene acetone.

HENRI BARBIER. 25

